Hydroquinone → HCID 67374020, compound

HRID 970945Notes

Reaction equation

HRID 970945 reaction equation
C1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H:8]([CH:4]2C=C1)[CH2:7]3.[CH2:11]([O:15][C:16](=[O:19])C=C)[CH2:12][CH2:13][CH3:14].C1(C=CC(O)=CC=1)O>>[CH2:11]([O:15][C:16]([C:6]12[CH2:7][CH:8]([CH2:4][CH2:5]1)[CH:9]=[CH:10]2)=[O:19])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 8846Butyl AcrylateHCID 15618652endo-Dicyclopentadiene

Product 1

HCID 67374020HCID 67374020, compoundYield 78%

Conditions

Temperature
190 °C

Procedure

DCPD (dicyclopentadiene, Aldrich, 180 mL, 1.34 mol), butylacrylate (Junsei, 500 mL, 3.49 mol), and hydroquinone (2.7 g, 0.025 mol) were put in a 2 L autoclave. After heating to 190° C., reaction was carried out for 5 hours while stirring at 300 rpm. After the reaction was completed, the reaction mixture was cooled down and transferred to a distillation unit. The reaction mixture was distilled at 1 torr using a vacuum pump at 80° C. to obtain the product (yield: 78%). The mole ratio (mol %) of the exo-isomers to endo-isomers of the product was 56.2:43.8.

Workup

  1. customreaction
  2. temperaturethe reaction mixture was cooled down
  3. distillationThe reaction mixture was distilled at 1 torr
  4. customat 80° C.

Sources & evidence

ORD record
ord-90f4c1169b6e49769aeaf60be7067696
Source dataset
uspto-grants-2007_12
Patent number
US07312285B2

Reaction notes

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